The reduction of 2-nitrophenylacetic acid to oxindoles promoted by SmI2 is reported for the first time. This reaction involving the reduction of nitro group proceeds through N-O bond cleavage and direct condensation with the neighboring carboxyl group. From a synthetic point of view, a new method for the synthesis of oxindoles in mild neutral conditions is developed.
{"title":"Synthesis of Oxindoles via SmI2-Promoted Reduction of 2-Nitrophenylacetic Acids","authors":"Pengkai Wang, Songlin Zhang","doi":"10.1055/a-2175-1008","DOIUrl":"https://doi.org/10.1055/a-2175-1008","url":null,"abstract":"The reduction of 2-nitrophenylacetic acid to oxindoles promoted by SmI2 is reported for the first time. This reaction involving the reduction of nitro group proceeds through N-O bond cleavage and direct condensation with the neighboring carboxyl group. From a synthetic point of view, a new method for the synthesis of oxindoles in mild neutral conditions is developed.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"67 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135690411","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kei Kitamura, Saki Ise, Tetsuto Tsunoda, Hiroto Kaku
We report herein an iterative assembly of chiral alcohol building blocks utilizing cyanomethylene trimethylphosphorane (CMMP)-mediated Mitsunobu reactions. 1,3-Benzodithiole tetraoxide (BDT) was used as the platform to prepare long-chain saturated compounds with multiple stereocenters en route to polyisoprenoid natural products. Selectively protected chiral 1,3-butanediols played a key role in iterative chain elongation for the construction of 1,5-dimethyl branched arrays with high stereocontrol.
{"title":"Iterative Assembly of Chiral Alcohols Utilizing CMMP-mediated Mitsunobu Reactions","authors":"Kei Kitamura, Saki Ise, Tetsuto Tsunoda, Hiroto Kaku","doi":"10.1055/a-2175-1271","DOIUrl":"https://doi.org/10.1055/a-2175-1271","url":null,"abstract":"We report herein an iterative assembly of chiral alcohol building blocks utilizing cyanomethylene trimethylphosphorane (CMMP)-mediated Mitsunobu reactions. 1,3-Benzodithiole tetraoxide (BDT) was used as the platform to prepare long-chain saturated compounds with multiple stereocenters en route to polyisoprenoid natural products. Selectively protected chiral 1,3-butanediols played a key role in iterative chain elongation for the construction of 1,5-dimethyl branched arrays with high stereocontrol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"3 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135734387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. 1 Introduction 2 Zweifel Olefination with New Organometallic Species 3 Zweifel Olefination with New Migrating Groups 4 Electrochemical and Photocatalyzed Zweifel Olefination 5 New Elimination and Migration Patterns of Zweifel Olefination 6 Zweifel Olefination in Natural Product Synthesis 7 Other Reactions Involving the Zweifel Olefination Mechanism 8 Conclusions and Outlook
{"title":"Recent Progress in Zweifel Olefination: An Update","authors":"Xin Li, Qiuling Song","doi":"10.1055/a-2172-1386","DOIUrl":"https://doi.org/10.1055/a-2172-1386","url":null,"abstract":"During the past several decades, Zweifel olefination has emerged as one of the most powerful and reliable tools for constructing C–C double bonds. This reaction features high efficiency, good versatility, nonuse of transition metals, and perfect stereospecificity, which make it superior to many other olefination methods. Since the summary of Zweifel olefination’s 50-years history was published in 2017 by Aggarwal et al., remarkable achievements have been made in terms of employing new organometallic species, proceeding through electrochemical or photochemical pathways, and furnishing new kinds of products. This short review summarizes and discusses the very recent progress in Zweifel olefination and its latest application in natural products synthesis. \u00001 Introduction \u00002 Zweifel Olefination with New Organometallic Species \u00003 Zweifel Olefination with New Migrating Groups \u00004 Electrochemical and Photocatalyzed Zweifel Olefination \u00005 New Elimination and Migration Patterns of Zweifel Olefination\u00006 Zweifel Olefination in Natural Product Synthesis \u00007 Other Reactions Involving the Zweifel Olefination Mechanism\u00008 Conclusions and Outlook\u0000\u0000","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"1 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80985763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720091","DOIUrl":"https://doi.org/10.1055/s-0040-1720091","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"28 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135047699","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Erratum - Synthesis of N -Propargyl Pyrrolylamides and Theoretical Study of Pyrrolylimide Reduction by NaBH 4","authors":"Sinan Basceken","doi":"10.1055/s-0040-1720090","DOIUrl":"https://doi.org/10.1055/s-0040-1720090","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"70 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84411865","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kankanala Naveen Kumar, Mouzma Mhate, Velayutham Ravichandiran, S. Swain
A photocatalyzed one-pot borylation of haloarene and reduction of aldehyde by cocatalysis of bis(pinacoloto)diboran/4-phenyl pyridine is reported. The reaction was carried out in a flow reactor by irradiating the reaction at 410nm, with residence time of 10 min. The method was successfully applied for the synthesis of tavaborole in a single step with 81% yield.
{"title":"Bis(pinacoloto)diboran/4-phenyl pyridine system for one-pot photocatalyzed borylation and reduction of aldehyde: synthesis of tavaborole in a flow reactor","authors":"Kankanala Naveen Kumar, Mouzma Mhate, Velayutham Ravichandiran, S. Swain","doi":"10.1055/a-2169-6200","DOIUrl":"https://doi.org/10.1055/a-2169-6200","url":null,"abstract":"A photocatalyzed one-pot borylation of haloarene and reduction of aldehyde by cocatalysis of bis(pinacoloto)diboran/4-phenyl pyridine is reported. The reaction was carried out in a flow reactor by irradiating the reaction at 410nm, with residence time of 10 min. The method was successfully applied for the synthesis of tavaborole in a single step with 81% yield.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"2 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74399390","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2023-09-01Epub Date: 2023-05-08DOI: 10.1055/a-2072-2754
Timothy J Barker, Andrew Bogatkevich, Dallas W Crowder, Sophia G Gierszal, Jacob C Hayes, Michael R Hollerbach, Richard W Russell
This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines.
{"title":"Reactions of Benzylboronate Nucleophiles.","authors":"Timothy J Barker, Andrew Bogatkevich, Dallas W Crowder, Sophia G Gierszal, Jacob C Hayes, Michael R Hollerbach, Richard W Russell","doi":"10.1055/a-2072-2754","DOIUrl":"10.1055/a-2072-2754","url":null,"abstract":"<p><p>This short review summarizes our laboratory's development of benzylboronic esters as nucleophiles. Activation of the benzylboronic ester is achieved by irreversible coordination of an alkyllithium Lewis base to form a nucleophilic benzylboronate. This boronate was found to react with aldehydes, imines, ketones and alkyl bromides. A copper catalyst was employed in reactions of the boronate with epoxides and aziridines.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"55 17","pages":"2639-2647"},"PeriodicalIF":2.2,"publicationDate":"2023-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10545366/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41171502","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720089","DOIUrl":"https://doi.org/10.1055/s-0040-1720089","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"26 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136243301","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Erratum - Synthesis and Optical Resolution of Inherently Chiral Fluorescent Calix[4]arenes and Their Application in Chiral Recognition","authors":"Fu Yang, Jun Luo, Yi-Chieh Chen, W. Chung","doi":"10.1055/s-0040-1720085","DOIUrl":"https://doi.org/10.1055/s-0040-1720085","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"42 2 1","pages":"e1 - e1"},"PeriodicalIF":2.6,"publicationDate":"2023-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84113399","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Heteroatom-embedded polycyclic aromatic compounds (hetero-PACs) are a class of organic compounds contributing to a variety of research fields such as materials science, chemical biology and so on. For applications using hetero-PACs, efficient preparation of hetero-PACs is essential. In particular, reactions transforming unfunctionalized aromatic compounds to hetero-PACs using appropriate heteroatom-containing aromatic compounds (π-extending agents) represent the most ideal way to prepare hetero-PACs. In this review, such heteroatom-embedding annulative π-extension (hetero-APEX) reactions including their reaction mechanisms and scope of substrates are described.
{"title":"Heteroatom-Embedding Annulative π-Extension (Hetero-APEX) Reactions: An Overview","authors":"Hideto Ito, Kou P Kawahara, Kenichiro Itami","doi":"10.1055/a-2169-4078","DOIUrl":"https://doi.org/10.1055/a-2169-4078","url":null,"abstract":"Heteroatom-embedded polycyclic aromatic compounds (hetero-PACs) are a class of organic compounds contributing to a variety of research fields such as materials science, chemical biology and so on. For applications using hetero-PACs, efficient preparation of hetero-PACs is essential. In particular, reactions transforming unfunctionalized aromatic compounds to hetero-PACs using appropriate heteroatom-containing aromatic compounds (π-extending agents) represent the most ideal way to prepare hetero-PACs. In this review, such heteroatom-embedding annulative π-extension (hetero-APEX) reactions including their reaction mechanisms and scope of substrates are described.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"798 1","pages":""},"PeriodicalIF":2.6,"publicationDate":"2023-08-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85445000","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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